We often assume that when people resist a new architectural direction, the answer is to explain better — clearer diagrams, more detailed documents, another walkthrough of the rationale. Diana Montalion spent twenty years perfecting this instinct. Then she realized she was Sisyphus: pushing the same rock up the same hills, and getting flattened every time it rolled back down.

The shift came at Kripalu, a retreat center where Diana had gone to rest from the exhaustion of constant explanation. The environment was overwhelmingly female — the opposite of the tech spaces where she'd spent her career, often as the only woman in the room. Learning happened there through movement and experience, not endless discussion. When her phone pinged with a question from the DDD Europe organizer — "You said this could be a workshop. What would you do?" — the answer suddenly felt obvious: design an experience, not an explanation.

What followed was a workshop that used the iceberg model to help participants understand how systems generate outcomes — using, as their subject, the fact that 91.88% of software developers are male. Nobody debated gender politics. Instead, working in groups, they modelled how a system produces that result, then designed a different system. Diana has run it four or five times now and learns something new every time. Back in her current role, she's applying the same logic to architectural change: rather than explaining until people understand, she tries things with them — and finds that people who were deeply resistant often pick up the ball and run with it once they've had the experience.

This conversation explores what it actually takes to move from explanation to experience — including how to work inside genuine uncertainty, how to interrupt cognitive patterns without steering people to your predetermined answer, and why facilitative leadership is, in Diana's words, genuinely harder than just telling people what to do.

Key Discussion Points

1. [00:01] The Sisyphus Pattern: Diana names her core habit — when facing resistance, explain more — and the exhaustion that finally forced her to question it
2. [03:00] The Kripalu Moment: A retreat centre, a predominantly female room, and a way of learning through experience rather than discussion that stops Diana cold
3. [04:00] The DDD Europe Workshop: How a well-timed ping from the conference organiser became the prompt to design an iceberg model workshop unlike anything she'd done before
4. [06:00] Modelling the Patriarchy: How asking teams to model a system that produces 91.88% male developers — not to debate gender, but to practise systems thinking — unlocks participation in a way no lecture ever could
5. [08:00] Architectural Miracles: In her current role, Diana catches herself falling back into "explain more" — and experiments with just trying things instead, with surprising results
6. [12:00] There Is Only Uncertainty: Diana's perspective on complexity, consent, and why promising important insight rather than solved problems is the honest deliverable
7. [22:00] Flying with the Flock: The delicate balance between listening, facilitating, and nudging — knowing when to interrupt a cognitive pattern without simply steering people to your own answer
8. [28:00] A Science and an Art: How facilitation is both deep listening and an energetic interruption of pattern — and why the hardest part is the work itself, once the friction is gone

Guest: Diana Montalion Hosts: Andrea Magnorsky, Kenny Schwegler

Part of the Stories on Facilitating Software Architecture and Design series from Virtual DDD.

welcome to stories of facilitating software

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design and architecture.

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Today we're here with Diana Monteon and

also with my usual co-conspirator Kenny.

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And so, Diana, please take

it away with your story.

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Diana: Okay, so, first of all, I love this

format because one of the things I'll say.

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not inherent in my story

is that storytelling

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one of the most powerful ways

to help an organization see

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a, a situation differently.

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And I just used it again.

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I wrote a Christmas story and

my current role that to try and

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just show that I was hearing what

people were saying and needing.

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Landed with so many more people than,

an architecture model would have.

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So I, I like that you've, it's very meta

that you've made this a story inside

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the experience because they both matter.

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so I guess this story that stands,

when you asked this, the thing

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that came screaming to mind is the,

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one of my.

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I'll say habits, not.

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Maybe The best habit is that when people

are confused or uncertain or when I

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don't really think they're hearing, I'm

trying to facilitate change and I don't,

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I feel like there's a lot of resistance.

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explain more.

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I think that what people need is more

words, more intake, more they need more.

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After 20 years, it was just exhausting.

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And also it felt like Sisyphus, I kept

pushing the same rock up the hill and

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it would roll back down and roll me

over and splat and I'd be a bug juice.

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And that's it.

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And why am I doing this?

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So I live near a place where, they do

like yoga, massage, stuff like that.

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And it's nice sometimes to take a drive

for an hour and go there and stay there

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for the day or stay there overnight.

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I was there just kind of resting

from a lot of work and I was

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in a little workshopy thing

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The facilitator said, oh yeah, you're not

here to think like, just you're quiet.

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Your brain, you're just

here to experience.

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I'm like, no, I'm, I'm, I'm

never, no, I'm never, I don't

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know how I don't have a button.

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If there's a button, let me know,

but I don't know where it is.

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but what I also noticed is that I was

having these experiences and it was.

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Predominantly people who, appear

to be or identify female and a few

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guys like people's partners go, or

individual guys, but that I work

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for 25 plus years in an environment.

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Exactly the opposite.

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know, for the first 10 or 15 years I

was often the only female in the room.

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And simultaneously when people.

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workshops or ways of learning.

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At k Palu is the name of the place there.

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It's very experiential.

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You're always experience something

moving through something.

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And in my day job, in my usual

life, in my system, science and,

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and software architect life.

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We don't have bodies really.

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We, we just, we just talk to,

we just talk to each other.

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Right?

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And we write code, like it

was, I just noticed how far

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apart these experiences were.

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Simultaneously, I had proposed

a talk for domain-driven

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design Europe, and I had said.

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I'd really like this to be a workshop.

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I think it would be a

much better workshop.

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And when I went back to my room after

having this enlightenment moment,

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literally the organizer of domain

driven design had pinged me while I

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was having this realization and said,

you said this talk could be a workshop.

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What would you do?

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What would you do?

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And I'm like, oh my gosh.

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I'm being asked the question

to actualize this, this in.

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Like, I'm not just realizing this.

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What would I do?

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And it's a place where I

tended to take risks Anyway.

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What I and my training partner decided

to do is we offered a workshop on.

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Understanding systems using

the iceberg model, right?

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The, mental models, the

structures and patterns that

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generate events in the system.

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We tend to focus on the events.

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There's a bug in production,

but not the fact that.

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Every system is designed

to get the results it gets.

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The call is coming from inside the

house and because of the, I usually work

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on digital, deep digital change with

organizations and architecting that.

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We have to be able to see how we are

generating the outcomes we don't want,

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and how do we generate the ones we do.

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And I'd really struggled

with how to do that.

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So we did is we used the iceberg

model, and we didn't call it this, but

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to model the patriarchy, meaning in

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90, well 92% of software developers

worldwide or male, but actually it's.

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91.88%.

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So not quite that bad.

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And if I had done a workshop to say, let's

talk about gender equality and like, first

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of all, who would've signed up for it?

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And secondly, people would bring all

their frames, their all their child.

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I would too.

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Like I would have ideas about that.

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It didn't do that.

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Instead, for the first half, we took

the iceberg model, the mental model

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structures and patterns and said,

okay, we're gonna work in groups.

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We're going to model a system

that generates that outcome.

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We want end up visibly male.

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That's what we want.

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And so we developed, we made stickies and

all the teams work together and did that.

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And then we said, okay, so let's flip it.

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want to design a system where you

can't tell if someone's a software

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engineer by looking at them like it.

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It looks just like the general population.

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I've since done that four times,

this workshop, four or five times.

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I learn so much every time I do it,

and people come up with all kinds of

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things that I never even thought of

before, and people have been very willing

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to engage in it it's experiential,

because we're having an experience.

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I'm not telling people what to think.

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I'm asking people to think together

about how something works and

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how it might work differently.

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So summarize now, the reason this state

really stayed with me, or the reason this

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idea came is that I'm in a role now where.

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I am with an organization that

I, I really, I really like and I

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really respect and I really like

the, the role that I'm doing.

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And part of that is getting from

a very crud based system and also

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practices to a system that can generate.

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Intelligence has the, has

temporal intelligence.

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All the things we think of with the

system, it's only been a few months, but

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I see myself making the same mistake of

like, if people don't really understand, I

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say more, I make more model I, I say more.

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This does not help.

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Also, when people are resisting,

they'll resist forever because they

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can find infinite ways I'm wrong or

they don't know whether I'm doing the

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right thing and I'm so much faster.

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Just instead designing an

experience, let's just try it.

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Let's do this.

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Let's just try it.

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And I have seen, I would say,

architectural Miracles in the last

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few months, or people who were very.

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resistant to a particular change for

reasons, but then they have an experience

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of it and they think it through for

themselves and then they go, wow, here

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are all the things I can do with this.

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And they pick up the ball and run with it.

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Now, that doesn't have to happen, but it's

a win if people have the experience and

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then say, this isn't gonna work, Diana,

and here are the reasons why that's great.

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Being wrong is wanna be wrong before I've.

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Cost a whole of time, energy, attention,

and money, banking on that, right?

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I want that.

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so this leadership as.

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I've come to think of it that this

type of leadership is facilitation

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and that facilitation is a type of

leadership that can be more effective,

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more impactful, and generate more

power in the sense of you have more

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impact, you have more positive impact.

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The legacy of the work.

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people for longer and wider, but it's

tricky to find because it doesn't look

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like it's supposed to look and you're

more vulnerable, like it leaves you

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in an unprotected space and you don't

know how people are going to react and

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that, that I think, is good for you to

have a bit of your feet on the ground.

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When you, when you try and do that,

like it's trickier in the beginning of

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a career to do that than it is later on.

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But you can always partner

with people who are doing it.

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And, and that's, that's another

thing, I guess, right, is

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pairing up, doing it together.

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Ha designing experiences, but

yeah, so facilitate experiences,

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especially if you feel like you

think you should explain more.

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Kenny Schwegler: Yeah, so recognizable

it, it reminds me a little bit of this,

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I talk about it often, some more, but it

reminds me of the Corporate Tribe Book

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of two Anthropologies in the Netherlands.

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It nothing to do in it,

but they say the same.

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they have this role called the Shaman

who creates experience or magic.

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Right?

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Whenever you're in such a workshop.

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And I think also Eric Evans mentioned,

right, the breakthrough and, and I

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think that's what you just mentioned.

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but what struck me is it's very uncertain.

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You're in an uncertain situation.

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How do you deal with that uncertainty?

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I think that's what scares well,

that scares me still to this day

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the most, stepping into that.

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Diana: I love that also that, it's

interesting you say that about,

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shaman or a tradition, right?

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Is that of the questions that

occurred to me around that time

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is like, what is at the core,

what our goal is, is wisdom like.

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Knowledge work.

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Wouldn't it be ideal if

knowledge work generates wisdom?

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And so this question of what is it to

be a wisdom teacher in this particular

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time of, of history the facilitation

aspect of what came to me as well.

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Like that I'm not sure I, you know,

have much to say about it, but it did.

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They like the points in this direction.

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I feel like if you have

that, so uncertainty.

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It's funny 'cause I was on a panel.

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One of the other speakers was

talking about the problem with

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uncertainty and, you know, complexity

and you know, and how you do.

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And I'm like, I don't get it.

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there is only

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That's all there is.

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Everything else is delusion.

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We're telling ourselves

we're making that up, right?

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Like, complexity.

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Uncertainty.

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This is the nature of everything.

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And so I think it's trying to discern

the difference between when you're

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trying to control that reality and

you can't, 'cause you really don't

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know what will happen as a result.

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when you are trying to act well

inside of uncertainty and complexity,

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like I definitely, it's not like,

oh, we're uncertain, but let's

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just leap off and see what happens.

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Like that's, you're not

architecting if you're doing that.

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But cons on the other side is also

not for me anyway, my work is often

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not going all the way to.

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a need for certainty because I,

I legitimately cannot, we can't,

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I can't facilitate us there.

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like the best thing we can become

certain of is this is the best possible

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idea, action, recommendation, direction

that we could come up with right now.

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And for me, that's enough.

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Like if we are like.

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There's like a 70% chance

this is a good direction.

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That's good.

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And this is the best we

could come up with right now.

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Yay.

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Kenny Schwegler: he, he always says

architecture is very easy if you are, if

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you have insight in the future, right?

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And, but it also reminds me a little bit.

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What, what, before we go to you, Andrea,

it always reminds me what you're saying

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about controlling the uncertainty.

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It's, it's like Avenger movie.

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You had the Hulk turn or Bruce Batter

turning into the Hulk, and him,

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how do you control not being angry?

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He says, I'm not.

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always angry.

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And I think that's what

you're explaining right?

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I'm always in uncertainty, so

I don't need to control it.

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Then it, then I can let it go

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Andrea Magnorsky: It is great

to know that Diana is the Hulk.

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I mean, it's like a, you know, an

interesting way to find out, but cool.

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Diana: I know from work, what's

the line from Thor, Ragnar?

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There's a friend from work.

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Kenny Schwegler: Yeah.

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Friend from

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Diana: yeah,

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Kenny Schwegler: Yeah.

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Diana: it's a friend from work.

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Andrea Magnorsky: Um, what

Dakota, I kind of was thinking

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that, that, yeah, definitely.

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I think uncertainty.

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Some organizations want to definitely

have the ideas that they are managing it.

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so actually my, my question to you

is like, how do you think people can.

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Get to like, you know, because

I understand how you can, like,

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for example, I do stuff my way

and can eat those stuff the way.

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And, but I think it's hard to, to kind

of try to think what is the, the, the,

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the pattern that is good so that we can

help organizations understand the fact

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that uncertainty is a fact of life.

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And that will be one question.

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And the second one is.

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I think if you talk to, to, some people

inside orgs and you say, Hey, let's do

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an experience, they'll will, like what?

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they will want some certainty of what

they will get out of the workshop

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and sometimes I say something

like, you will learn something.

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Um, so, so can you talk about those

kind of two areas when it comes to

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running this type of experiences?

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Diana: Yeah.

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And it, they go together and, and first

I think I wanna say, 'cause I know this

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is, this comes up, comes up a lot, this,

especially if I, when I do workshops and

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it's like, you cannot lead a horse to

water and you cannot make them drink.

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if, if somebody's like, no, and we

want this and we need this and we're

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not gonna take a risk and all of that.

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I personally don't know what to do in that

like, 'cause it involves consent, right?

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All facilitation involves consent.

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That's the difference between facilitation

and command and control, right?

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And I can get a smaller bit of consent.

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I can ask for consent for something.

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the person is willing to consent to,

but you can't do it trick or what?

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I mean you can, but

it's counterproductive.

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So part of my answer to that is if the

organization is like, I need to know like

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what the core deliverables are and what

we get and what's the measurable metric

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for the do this experiment all the time.

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I don't know that I could

necessarily be effectively

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experiment in that environment.

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I could try, but um.

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A little bit of willingness,

I think is part of the, is

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the doorway, but a little bit.

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So for me, where I focus is not to have

these conversations because no one, no.

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I mean, in tech, I could have

philosophical conversations all day,

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but no one wants to philosophical

conversations with me, and it's

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also not really what my point is.

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I focus on.

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the organization most wants.

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So in my current situation, for

example, when I listen to product, you

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know, strategizing vision and really

understanding the, the people that we

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serve, there are things that are really

clearly keep coming up for them, right?

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So the thing is.

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Nobody knows how I, I don't know

how to concretely describe exactly

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what we would make in tech to

give them the thing they want.

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They're not even sure that they understand

completely exactly how users will do

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things, exactly what it is they want.

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There is inherent uncertainty,

but there's also a tremendous

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desire to find out because they've

identified this as really important.

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So within that, I try to structure a, to

describe what it is we know, what is it

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that we're really comfortable with, and

what are the, like, if I'm gonna make

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a recommendation, what convinced me?

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What do we know?

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What, what data do we have?

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What, what certainty do we have?

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To back up the encouragement

to take one step.

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So we know this, we know that,

you know, this is really valuable

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and we want to take the stretch.

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then what could we try?

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What's the experience?

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What do we not know and how

would we, here's what I would

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suggest, how we find out.

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And the deliverable is valuable knowledge.

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Valuable information.

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You wanna go in this direction, but

we're not entirely sure how I can

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come back and give you something

concrete that doesn't totally answer

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it, but it does give you something.

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You know, you need some information,

you need to move forward.

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Most of the time I can make

something happen inside of that

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space, outside of that space.

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People have to already understand

the value of these approaches, or

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it'll just be an endless debate.

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So picking an area where there is already

acknowledgement of complexity and not

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promising to solve a problem, but instead

promising to deliver important insight.

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that to be the most

successful, the hard part is.

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don't know what to do.

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Like I, like I have to make

up an experience and I have

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to know what might help.

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That's not easy.

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So I guess I think I wanna

end with this idea that.

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Um, we think, we think for most of my

career, the hardest part has been this.

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How do you get an organization repeat?

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How do you lead a horse to water?

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How do you do this?

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I'm at the place in my career now and, and

with the organization I'm in where it's

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actually the work that's the hardest like.

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When there isn't friction, when you

can facilitate, you discover that

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facilitative leadership is way harder

than just telling people what to

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do because you are uncertain too.

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You are experimenting too.

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You are vulnerable right along with them.

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And I think that, that's where we

really grow our skillset is when we

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really have to take a risk and, and

figure out what would, what's the one,

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one thing we could do would give us

more confidence in a situation where

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there's a thousand things we could do.

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It's hard.

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Kenny Schwegler: I think you

said something interesting

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because I was at your session

at DDD Europe, by the way, and,

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Diana: were.

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Yeah, you were.

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Kenny Schwegler: afterwards,

I used the iceberg

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Diana: You said safe though.

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You, you said the solution

to the 91% is safe.

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That would fix it.

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Kenny Schwegler: I made it.

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Oh yeah, that was a joke.

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Uh, but I went to the company with

someone else, where I, where I'm currently

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still in, and I started mapping this.

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And you said something very interesting

because you saw a pattern arising

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just by modeling it out for yourself.

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I'm not sure if you did that, but

I did that and I saw the same thing

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happening and it reminded me of.

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DDD language and what you can get

out of that is use their language,

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use what they already know, use

what, what's repetitive, and if you

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can, merge the experience into that.

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Is that what you're saying?

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If I, in short did.

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Diana: Well, it's the,

it's the, um, it's the.

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It's the when we're do, when we're, when

we're starting having an experience,

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we're starting with all of our own.

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Like if our cognitive space is

just all the stuff we've put

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in our mental garage, right?

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This is all the stuff we

have that if people have to.

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abandon their garage and go into

a completely different space with

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tools that they don't recognize.

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It's, it's too, it's too, there's

too much going on to then.

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Use those tools to come up

with a new idea, like come up

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with, you know, with a frame.

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But if you can focus on something that we

generally all have at least some aspects

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of these in our garage and reshape them.

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But the trick is you can't

just move them around.

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That's just changing seats on the Titanic.

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You still have to build

something different.

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From those materials, right?

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So that's the tricky piece is the,

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the, if people can draw on their own

experience, you'll get more value out of

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doing it because you, it, everybody, it

brought valuable experience into the room.

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but.

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It's not just moving

that experience around.

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Right.

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My cat is, has decided to,

she joins every meeting, but

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Kenny Schwegler: an

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Diana: this one.

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Kenny Schwegler: in a

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Andrea Magnorsky: Yeah, she is definitely,

uh, what, what I'm, what I'm hearing

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also is that you are basically very

focused on listening on what the outcomes

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that they really value are and trying

to kind of share the common ground.

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I think you're kind of, uh, like

you, what I ex I understand by

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what you explained is that you.

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Listen to people and try to tell the, try

to replay, especially the parts that are

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common and kind of say, okay, these two,

you know, your experience, Kenny, of what

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is needed and what is the problem and

your experience there, and whoever else

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is in the room or the garage or whatever.

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And these are the bits that,

we are sharing and it seems

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like we're going over there.

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That's the outcome.

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Somewhere there is that, and you're kind

of iterating on that until you find it.

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That's what I'm getting.

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Is that what you're talking about?

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Diana: A, a little.

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A little.

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Yes, but all yes.

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definitely.

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So

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Andrea Magnorsky: I.

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Diana: wasn't doing that, nothing

good would be happening for sure.

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Right.

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Like and this is where like,

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I give talks very different now than

I did 20 years ago because my role

408

in that room feels very different.

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And it's more in line with what

you're saying, like, we are here

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together to do a thing, as opposed

to I'm presenting something right?

411

Like there's, that personas changed.

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also what I would add to that

though is that my role, the

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expertise that I am developing.

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Is, it's interesting 'cause we, we

started talking about wisdom, things

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like this, that these are, cognitive

patterns are energetic patterns, right?

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They're, we have an idea, a

belief, something we value.

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When we have an, when we think

of something, our minds will go.

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In a particular familiar direction.

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So for example, working with teams,

going from Cru, a mo, a crud, monolith

420

to asynchronous and microservices,

it's very challenging because our

421

thinking is very tightly coupled.

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So when we build the microservices, like

we architect them to be tightly coupled.

423

So it is, it's listening and it's.

424

Facilitating and going and

trying not to add friction,

425

but there is definitely a very,

426

I think, important, Nudging that,

that you're list energetically, you're

427

looking for the places where this is

gonna go down the same path, right?

428

Like the same.

429

This will

430

Andrea Magnorsky: No.

431

Diana: thinking that even though

it seems like new thinking, we're

432

going to end up in the same place.

433

And the, the places where you can ask

a different question or do a different

434

thing, but that also requires a little

bit of, thinking about what the change is.

435

Like if people are going in a particular

direction and you're facilitating to

436

nudge them in a different direction.

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If you have no idea where that

direction is, then you can't do that.

438

Right?

439

But at the same time.

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You don't know that you are just someone

else in the room with an, with a thought

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about what the right outcome is, right?

442

And so if you're just gonna bring them

to your idea, you might as well just tell

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them your idea and tell 'em go do it.

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Like that's the honest, like that's

the intellectually honest thing.

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And every once in a while I am

like, 'cause I said so do this.

446

'cause I, so every once in a very

great while, but it's very, very rare.

447

So it is a little bit like a flock

of birds where you have to be.

448

Grounded enough in, in the space, enough

to be flying with the, the, the flock of

449

birds while you're facilitating, right?

450

If you're trying to marshal it, it

won't work, and if you're trying

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to control it, it won't work.

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But also if you turn off your brain and

just flow with it to kind of go and you're

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not actually adding a little tension

where it should go, then, and sometimes

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that's exactly what you wanna do.

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Sometimes in facilitation, you are

just helping people articulate.

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What's going on?

457

That's great.

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I'm not against that at all.

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for me it is more usual nowadays

that we're facilitating towards an

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insight that we haven't had yet.

461

then, so it's looking for those

opportunities to open a window

462

differently, might work, might not work.

463

so it's, both a science and an art.

464

I guess It's both listening and

also an energetic, Interruption of

465

pattern in some way that is helpful

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Andrea Magnorsky: Yeah,

I think, I think that,

467

Diana: when it

468

Andrea Magnorsky: yeah.

469

Yeah.

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I love that the, I see them

myself and I'm that, you know.

471

People listening will see them too.

472

I think that's a, that's a beautiful

place to, to, close this, story.

473

thank you very much, Diana for

joining us, Kenny for wellbeing, here.

474

So we are here together

and, well, that's it.

475

Thank you very much.

476

Bye bye.